diazoamino coupling of a 4-sulfobenzenediazonium salt with some cyclic aminesdiazoamino 4-sulfobenzenediazonium的耦合与一些循环胺盐.pdfVIP

Molecules 2002, 7, 706-711 molecules ISSN 1420-3049 Diazoamino Coupling of a 4-Sulfobenzenediazonium Salt with Some Cyclic Amines † * Marytė Kažemėkaitė, Zita Talaikytė, Gediminas Niaura and Eugenius Butkus Institute of Biochemistry, Mokslininku 12, Vilnius 2600, Lithuania, Fax (+370) 2 729186. †e-mail: zitat@bchi.lt * Author to whom correspondence should be addressed; e-mail: butkus@bchi.lt Received: 28 August 2002; in revised form 17 September 2002/ Accepted: 19 September 2002 / Published 30 September 2002 Abstract: Preparation of several novel potassium salts of 4-substituted aminoazo- benzenesulfonic acids by the simple and convenient reaction of insoluble 4-sulfo- benzenediazonium chloride with some (hetero)cyclic amines of various ring sizes is reported. The compounds obtained have shown potential antiinflammatory activity in biological testing. Key words: amines, diazoamino coupling, 4-sulfobenzenediazonium chloride, triazenes Introduction Aromatic aminoazo derivatives or triazenes represent a stable aryl diazonium ion source and are thus a class of nitrogen-containing compounds useful for synthetic transformations [1]. In a well- known classical synthesis the aromatic diazoamino system is formed in the reaction between a diazonium cation and the nucleophilic nitrogen atom of an amine. Usually the diazonium salt involved is not isolated, and an acidic aqueous solution of this reagent is e